Abstract
Anodic oxidation of cyclopentanone and cyclohexanones in a mixed solvent of CF3COOH and CH2C12 containing triethylamine led to unusual rearrangement to give selectively γ-valerolactone and a mixture of γ-and δ-lactones, respectively.
Anodic cleavage of a bond between the carbonyl carbon and the adjacent carbon of cycloalkanones followed by Wagner-Meerwein rearrangement and re-cyclization may be proposed as one of the most plausible reaction mechanisms.
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References
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Nishiguchi, I. (1998). Unusual Rearrangement by Anodic Oxidation of Cycloalkanones in the Presence of Trifluoroacetic Acid. In: Torii, S. (eds) Novel Trends in Electroorganic Synthesis. Springer, Tokyo. https://doi.org/10.1007/978-4-431-65924-2_57
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DOI: https://doi.org/10.1007/978-4-431-65924-2_57
Publisher Name: Springer, Tokyo
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